Buying a Business While Working Full-Time & Raising 7 Kids (No Margin for Error) with Michael Simpson

Buying a Business While Working Full-Time & Raising 7 Kids (No Margin for Error) with Michael Simpson

March 18, 2026 · 40 min · Episode 368

About this episode

Michael Simpson shares his challenging experience of buying a business while managing a full-time military career and a large family.

What does it actually look like to buy a business with zero margin for error? No safety net. No backup plan. A full-time military career, seven kids at home, and a lender who pulled out mid-deal. That's exactly where Michael Simpson found himself. In this episode, Jaryd Krause sits down with Michael Simpson - a National Guard serviceman who bought an 18-year-old e-commerce business using SBA financing, survived a near-collapse due diligence process, and came out the other side with a real, running business. But he's not here to tell you it was amazing. He's here to tell you the truth. Here's what's covered: 🏦 How he lost his SBA lender mid-transaction - and saved the deal in 48 hours 💀 The post-closing liquidity trap that blindsides almost every first-time buyer 😬 Why buying slightly bigger might have changed everything 📈 The unglamorous growth playbook keeping a 20-year-old business moving forward This isn't a success story wrapped in a bow. It's something far more valuable - an honest account of what buying a business really costs you. In money, stress, and lessons you can't learn anywhere else. If you're thinking about buying your first business, this might be the most…

People in this episode

Host: Jaryd Krause

Guest: Michael Simpson

Topics covered

Keywords

Mentioned in this episode

Organizations: SBA, National Guard

Places: e-commerce

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